Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Bicyclic (Alkyl)(amino)carbenes (BICAACs): Stable Carbenes More Ambiphilic than CAACs

Bicyclic (Alkyl)(amino)carbenes (BICAACs): Stable Carbenes More Ambiphilic than CAACs
Max M. Hansmann, Mohand Melaimi, Rodolphe Jazzar, Eder Tomás-Mendivil, Cory M. Weinstein, Guy Bertrand
A straightforward strategy allows for the synthesis of storable bicyclic (alkyl)(amino)carbenes (BICAACs), which feature enhanced σ-donating and π-accepting properties compared to monocyclic (alkyl)(amino)carbenes (CAACs). Due to the bicyclo[2.2.2]octane skeleton, the steric environment around the carbene center is different from that of CAACs and similar to that observed in classical N-heterocyclic carbenes. The different electronic properties of BICAACs as compared to CAACs allow for ligand exchange reactions not only at a metal center, but also at main group elements.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b04640

DOI: 10.1021/jacs.7b04640

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